1-(4-Chloro-phenyl)-4,4,4-trifluoro-3-trifluoromethyl-but-2-en-1-one | 35443-99-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-Chloro-phenyl)-4,4,4-trifluoro-3-trifluoromethyl-but-2-en-1-one
• 英文别名: Crotonophenone, 4'-chloro-4,4,4-trifluoro-3-(trifluoromethyl)-；1-(4-chlorophenyl)-4,4,4-trifluoro-3-(trifluoromethyl)but-2-en-1-one
• CAS: 35443-99-3
• 化学式: C₁₁H₅ClF₆O
• 分子量: 302.604
• InChiKey: AGWQEAPKCXRCEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(4-Chloro-phenyl)-4,4,4-trifluoro-3-trifluoromethyl-but-2-en-1-one 在 sodium hydride 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 2.0h， 生成 5-(4-氯苯基)-2-[(2-羟基乙基)甲基氨基]-3-(三氟甲基)呋喃
  参考文献：
  名称：

  Partially Fluorinated Heterocycles from 4,4-Bis(trifluoromethyl)-hetero-1,3-dienes via C–F Bond Activation – Synthesis of 2-Fluoro-3-(trifluoromethyl)furans

  摘要：

  An efficient synthesis of 2-fluoro-3-(trifluoromethyl)furans was developed. Keystep of the reaction sequence is a [4 + 1] cycloaddition reaction of tin(II)chloride to 4,4-bis(trifluoromethyl)-1-oxabuta-1,3-dienes. At elevated temperatures the tin heterocycles are transformed into 1-aryl-4,4-difluoro-3-(trifluoromethyl)but-3-en-1-ones which on treatment with sodium hydride in dry DMF give 2-fluoro-3-(trifluoromethyl)furans. The single fluorine bound to C-(2) can be readily replaced by various N-, O-, S-, and C-nucleophiles and dinucleophiles.

  DOI：

  10.1007/s00706-007-0587-4
• 作为产物：
  描述：

  在 吡啶 、 盐酸 、 三氟乙酸酐 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 5.0h， 生成 1-(4-Chloro-phenyl)-4,4,4-trifluoro-3-trifluoromethyl-but-2-en-1-one
  参考文献：
  名称：

  Synthese von 4,4-Bis(trifluormethyl)-1-oxabuta-1,3-dienen

  摘要：

  Silyl enol ethers (1) and hexafluoroacetone (2) react to give O-silylated aldol adducts 3 which, after desilylation with methanol/hydrochloric acid, are transformed into 4.4-bis(trifluoromethyl)-1-oxabuta-1,3-dienes (5) on treatment with trifluoroacetic acid anhydride/pyridine.

  DOI：

  10.1002/prac.19923340304

文献信息

• Synthesis of 3-trifluoromethylfurans from β,β-bis(trifluoromethyl)α,β-unsaturated ketones and tin(<scp>II</scp>) chloride
  作者：Klaus Burger、Brigitte Helmreich

  DOI：10.1039/c39920000348

  日期：——

  A new building block strategy for the synthesis of 3-trifluoromethyl-substituted furans 9 and 10 is described from β,β-bis(trifluoromethyl)α,β-unsaturated ketones 2via reductive fluoride elimination and 1,5-electrocyclization with elimination.

  报道了一种新的合成3-三氟甲基取代呋喃9和10的模块化策略，通过β,β-双(三氟甲基)α,β-不饱和酮2经过还原氟消除和消去1,5-电环化反应实现。
• 3-Trifluoromethylthiophens from hexafluoroacetone
  作者：Klaus Burger、Brigitte Helmreich、Oliver Jendrewski

  DOI：10.1016/0022-1139(93)02906-u

  日期：1994.1

  A one-pot procedure for the synthesis of 2-fluoro-3-trifluoromethyl- substituted thiophens 6 from 1-aryl-4,4-difluoro-3- trifluoromethylbut-3-en-1-one (3) and phosphorus pentasulfide is described. The fluorine atom at C-2 of compounds 6 undergoes nucleophilic displacement reactions.

  描述了一锅法从1-芳基-4,4-二氟-3-三氟甲基丁-3-烯-1-酮（3）和五硫化二磷合成2-氟-3-三氟甲基取代的噻吩6的方法。化合物6的C-2处的氟原子经历亲核取代反应。
• An efficient synthesis of ethyl 4-aroyl-5-trifluoromethylpyrazole 3-carboxylates
  作者：Jörg Cyrener、Christa Lauterbach、Klaus Burger

  DOI：10.1016/0022-1139(96)03397-0

  日期：1996.5

  Ethyl 4-aroyl-5-trifluoromethylpyrazole 3-carboxylates have been synthesized from readily available 4,4-bis(trifluoromethyl)-1-oxabuta-1,3-dienes (vinyl ketone) and ethyl diazoacetate and subsequent thermally induced elimination of trifluoromethane in good yield.

  由易于获得的4,4-双（三氟甲基）-1-恶唑-1,3-二烯（乙烯基酮）和重氮乙酸乙酯合成四乙基4-芳酰基-5-三氟甲基吡唑3-羧酸酯，然后通过热诱导消除三氟甲烷。良品率高。
• Synthesis of 2-Fluoro-3-trifluoromethylthiophenes and 3-Trifluoromethylthiophenes from Hexafluoroacetone
  作者：Klaus Burger、Brigitte Helmreich、Vera Ya. Popkova、Lev S. German

  DOI：10.3987/com-94-s(b)82

  日期：——

  The transformation of bis(trifluoromethyl)-1-oxabuta-1,3-dienes (1) - available from hexafluoroacetone - into 2-fluoro-3-trifluoromethylthiopheneses (9) via 4,4-difluoro-3-trifluoromethyl-3-buten-1-ones (5) is described. The fluorine atom at skeleton position 2 of the thiophenes (9) is readily displaced by various nucleophiles.
• Synthese von 4,4-Bis(trifluormethyl)-1-oxabuta-1,3-dienen
  作者：Klaus Burger、Brigitte Helmreich

  DOI：10.1002/prac.19923340304

  日期：——

  Silyl enol ethers (1) and hexafluoroacetone (2) react to give O-silylated aldol adducts 3 which, after desilylation with methanol/hydrochloric acid, are transformed into 4.4-bis(trifluoromethyl)-1-oxabuta-1,3-dienes (5) on treatment with trifluoroacetic acid anhydride/pyridine.